---
title: "Confidence Is a Metric: The Enablement Survey That Ties Training to Revenue"
episode: 149
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Chad Trabucco"
guest_title: "Director of Enablement Business Partner Strategy and Activation, Boomi"
date_published: 2026-11-02
date_modified: 2026-11-09
duration: 00:54:19
word_count: 9321
topics: ["sales-enablement", "sales-leadership", "revenue-operations", "ai-in-gtm"]
canonical_url: https://www.leanscale.team/knowledge/podcast/chad-trabucco-boomi-confidence-is-a-metric/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# Confidence Is a Metric: The Enablement Survey That Ties Training to Revenue

_Chad Trabucco on the quarterly rep-confidence survey he calls the voice of sales, why enablement has to invest in frontline managers, deal green lights and coach camps, the leading metrics that tie training to conversion, ACV and win rate, what a ramped rep actually looks like, and AI role play as the warm-up before a live call_

**Episode 149 · The LeanScale Podcast**  
Chad Trabucco, Director of Enablement Business Partner Strategy and Activation, Boomi · Hosted by Anthony Enrico  
Published November 2, 2026 · Updated November 9, 2026 · 00:54:19  
Canonical: https://www.leanscale.team/knowledge/podcast/chad-trabucco-boomi-confidence-is-a-metric/

**Topics:** Sales Enablement · Sales Leadership · Revenue Operations · AI in GTM


## Executive summary

Chad Trabucco is Director of Enablement Business Partner Strategy and Activation at Boomi, where he leads a global team of enablement partners embedded in commercial, enterprise, solutions engineering and customer success. He got into enablement about 11 years ago by answering RFPs, which led to his role as the founding enablement hire at Glint. Per the show notes, he helped take Glint from roughly $1M in ARR to about $60M at its acquisition by LinkedIn and ran its win-loss program for four straight years, then built enablement from zero at Dixa and at Guru.

The episode answers a question every enablement leader eventually hears from finance: what is this team worth? Chad's answer starts with a number most teams never measure. At Glint he hypothesized that a more confident seller would be a more effective seller, and that confidence gave enablement a leading measure it could influence and connect to the quarter's revenue results. He runs what he calls the voice of sales at the start of each quarter, looks back at what was rolled out, and tracks the change. He also asks managers how confident they are in their teams, and treats any disagreement as a prompt for discovery and a co-built program. At Guru, a survey he ran in his first couple of weeks exposed a gap with the HR persona, and he convinced leadership to do persona training before the new sales methodology they had planned.

Host Anthony Enrico presses on why so much of Chad's attention goes to managers. Chad says the seasoned managers at Glint mostly needed visibility, but newer managers on fast-scaling teams, often former top AEs, need a shared foundation: a sales process that is both written and taught. His current work includes stage-by-stage green lights built into managers' calendars, peer-to-peer coach camps, and agents and alerts in Slack and Salesforce that surface coaching opportunities. A no-surprises rule for managers and predictable rituals give enablement places to repeat a message seven times, seven ways.

The sharpest section is how enablement proves its value. Chad says every time he has tied a leading metric to the revenue outcomes leadership cares about, he has found success. At Guru, after a series of AI trainings, AI came up in what he recalls as about 20% of calls and then 60% within two to three months, and ACV doubled over that period. He calls this kind of link correlation, not always causation. In the win-loss program he ran at Glint, a persistent decline against two top competitors redirected a sales kickoff toward peer-to-peer competitive training, and win rates rose 10 and 15 points the following quarter. Anthony supplies the math: on a $20M plan converting 20% of pipeline, one point of conversion is another $1M in bookings, and the same math runs the other way.

The last section covers ramp and AI. Chad defines ramp by consistent behavior rather than product knowledge, wants leadership to agree on the definition up front, and uses time to the fourth or fifth deal as an early signal of momentum. He builds onboarding around the sales process so new reps can recall what to do at each stage. On AI, he is analyzing call data directly from data warehouses and sees role play as the warm-up before a live call. The episode suits enablement leaders, CROs, RevOps leaders and founders who need to justify enablement investment or scale frontline management.


## Key takeaways

1. **Confidence is a leading metric enablement can control** — Chad's starting hypothesis at Glint was that a more confident seller would be a more effective seller. Confidence also gave enablement a leading signal it could influence and then connect to the quarter's revenue results. He runs the survey, which he calls the voice of sales, at the beginning of each quarter, looks back at what was rolled out in the last quarter, and tracks the change.
   _Why it matters:_ Asked repeatedly, the survey shows where sellers need help and whether enablement is moving the needle. Chad says the trend is what makes the data useful, and he pairs it with win-loss data so the company's view and the field's view can be triangulated.
   _For:_ Sales Leaders, Revenue Executives, RevOps Leaders

2. **Survey managers too, then dig into the disagreement** — Chad also asks managers how confident they are in their team's ability to do specific things. When a rep's confidence is high and the manager's is lower, he does what sellers are told to do: more discovery, probing for the pain, and tying it to value.
   _Why it matters:_ The gap becomes a program built together with that manager. Afterward enablement can show the pain, how it was solved and what comes next. Chad says that co-build is what turns enablement from enforcement into empowerment.
   _For:_ Sales Leaders, Revenue Executives

3. **Let survey data reorder the roadmap** — When Chad arrived at Guru, leadership was already prepared to bring in a new sales methodology. His survey, run within his first couple of weeks, showed an immediate gap in speaking to the HR persona, which was core to going larger in accounts and selling across the full company.
   _Why it matters:_ He told leadership the methodology would be less effective without the persona work first. Persona training ran first, with reps scored on how they played both the seller and the buyer. Chad says it also built trust with the field.
   _For:_ Sales Leaders, Revenue Executives

4. **The fundamentals slip, so repeat them seven times, seven ways** — Chad has not found a common confidence gap across companies in the survey data. His gut-feel theme is the fundamentals, such as running an upfront contract or saving five minutes to close a call and document next steps. Enablement can assume that something trained last quarter is now standard, and that is not always the case.
   _Why it matters:_ A sales leader Chad cites says you have to hit people seven ways with seven different messages before things sink in. Anthony adds that people need to be reminded more than they need to be told or taught, especially when a scaling company keeps adding new reps.
   _For:_ Sales Leaders, Founders

5. **No surprises for managers, and rituals reps can plan around** — Chad meets every two weeks with the leaders of each group he supports, gives them communications to share, and briefs their managers before anything rolls out. He calls no surprises to the manager group one of the things enablement does have control over. He also relies on rituals: a monthly enterprise town hall and quarterly competitive, product and pricing training at Boomi, plus segment and regional meetings and consistent Slack, email and newsletter communication.
   _Why it matters:_ Rituals give enablement more places to repeat a message and let reps keep their attention on customers. They can also be re-leveraged for ad hoc requests, which Chad frames under a common theme so that the reason and the what's-in-it-for-them are clear.
   _For:_ Sales Leaders, Revenue Executives

6. **New managers need a written and taught sales process** — Chad says the seasoned managers at Glint needed visibility more than enablement. With teams scaling quickly and a cohort of newer managers, often former top AEs, enabling them on the desired behaviors becomes more important. He cites a CRO's simple framework: have a written and a taught sales process, and the team will be more predictable.
   _Why it matters:_ Chad tells enablement and ops people to watch for teams drifting from that process, because different interpretations produce different results. Anthony notes that manager enablement compounds, since managers do the day-to-day reinforcement in coaching and deal reviews.
   _For:_ Sales Leaders, Revenue Executives, Founders

7. **Green lights codify behaviors, not stage durations** — Chad's team takes the signals in its data that move deals from one stage to the next the quickest and defines the green lights that have to happen at every stage: the behaviors, the outcomes, the activity. He says measuring that a stage takes 20 or 40 days misses the behaviors that drive it.
   _Why it matters:_ The green lights are documented, trained to the managers and built into their rhythm in almost a calendar format, so the sales process also defines what a manager's week looks like.
   _For:_ Sales Leaders, RevOps Leaders

8. **Coach camps and always-on alerts extend manager development** — A colleague who used to be on Chad's team now focuses exclusively on managers and runs what he calls coach camps, with surveys and analysis beforehand so topics are relevant. Newer managers learn from seasoned ones, and those who know the latest tooling teach those who have been around longer. Chad's team is also building agents and alerts into Slack and parts of Salesforce that flag opportunities to coach.
   _Why it matters:_ The aim is signal in the noise: the one priority to coach for a particular rep, based on the framework, the process and recent calls. Chad describes this always-on coach as something they are leaning into and still exploring.
   _For:_ Sales Leaders, RevOps Leaders

9. **Tie a behavior change to the revenue number** — Chad says every time he has captured a leading metric linked to revenue outcomes, he has found success. At Guru, around the arrival of ChatGPT, a series of AI trainings took AI mentions from something like 20% of calls to 60% within two to three months, and ACV doubled over that period.
   _Why it matters:_ Chad is explicit that such links are correlation and not always causation. Sharing incremental progress regularly means a headcount request does not have to become one big business justification.
   _For:_ Revenue Executives, RevOps Leaders, Sales Leaders

10. **Competitive win rate changed what a kickoff was for** — In the win-loss program, kept in a spreadsheet before Gong, Chad tracked win rates against the top five competitors each quarter. The initial direction for a sales kickoff was more sales training, but he could show the CRO a persistent decline against two of the biggest competitors. The kickoff instead had reps explain how they beat those competitors.
   _Why it matters:_ The following quarter win rates rose 10 points against one competitor and 15 against the other, at an ACV Chad puts in the six-figure range. He says peer teaching also makes the training feel attainable to the field.
   _For:_ Sales Leaders, Revenue Executives, Marketing Leaders

11. **One point of conversion can be a million dollars, and the math runs both ways** — Anthony's example: on a $20 million bookings plan at a 20% conversion rate, you need $100 million of pipeline. Improve conversion by one point on the same pipeline, reps and pricing and you add $1 million of bookings. If new reps drift and conversion dips, the same math can cost you millions.
   _Why it matters:_ Anthony says enablement does not need to claim full credit, only to show that it influenced the number. Chad adds that enablement takes reps out of the field, so it has a responsibility to show the impact of that time.
   _For:_ Revenue Executives, Founders, RevOps Leaders

12. **Get dirty with the data** — Chad says he has never been anywhere, including places with sophisticated RevOps teams, where enablement could measure what it wanted as quickly as it wanted. Enablement people often don't come from a data background, so he has had to get creative at every company, for example measuring time to first deal directionally and measuring the earlier period the same way.
   _Why it matters:_ He names this as the main challenge of his career and also its strongest accelerant. Being able to stand behind a number and explain how it was measured is what lets enablement speak to leadership.
   _For:_ RevOps Leaders, Revenue Executives

13. **Repeat questions are a training barometer** — Beyond checking whether trained phrases show up in conversation intelligence, Chad has measured repeat questions in Slack. With AI you can ask an LLM how often the same or similar questions appear in a channel, then check whether the rate falls after a training.
   _Why it matters:_ Chad has seen a trend at multiple companies: when repeat questions fall in Slack, email and Jira, the remaining questions become more deal specific and nuanced. It also lightens the load on the subject matter experts answering in those channels.
   _For:_ RevOps Leaders, Sales Leaders

14. **Ramp is consistent behavior, not product training** — Anthony says many people call a rep ramped once they can walk through the product and pitch deck. Chad looks at which reps are consistent quarter in and quarter out, then studies the behaviors behind that: time on the phone, self-sourced pipeline, pipeline inspection, requalification. He also says leadership has to agree on what ramp and time to first deal mean, or you end up in knife fights later.
   _Why it matters:_ Chad uses time to the fourth or fifth deal as an early flag for intervention, and builds onboarding around the sales journey rather than a pile of content, so reps can recall what to do at each stage.
   _For:_ Sales Leaders, RevOps Leaders, Founders

15. **AI role play is the stretch before the sprint** — Chad sees companies leaning into platforms that ingest your methodologies and call data so that reps, SDRs and even CS teams running QBRs can practice outside live deals. A sales leader described it to him as stretching before a sprint.
   _Why it matters:_ Practice protects scarce pipeline while reps work out the kinks. Chad says the people leaning into it at Boomi are already the top performers, because they are still hungry and take every chance to get better.
   _For:_ Sales Leaders, Revenue Executives, Customer Success


## Frameworks

### Voice of Sales Confidence Survey (01:52)

**Definition:** A survey run at the beginning of each quarter that asks sellers how confident they are on what enablement rolled out, creating a leading measure enablement can influence and connect to revenue results.

Chad started it at Glint on the hypothesis that a more confident seller is a more effective seller. He looks back at the prior quarter's programs, measures confidence and watches the change. He has not cohorted it by team, preferring to clean up by title on the back end. Paired with win-loss data, it lets enablement triangulate the company's view and the field's view.

### Seven Times, Seven Ways (08:08)

**Definition:** People need to be hit seven ways with seven different messages before something sinks in.

Chad credits a sales leader with the phrase and uses it against the assumption that something trained last quarter is now standard. Rituals such as quarterly training, town halls, Slack and newsletters give enablement the places to deliver those repetitions.

### No Surprises (10:55)

**Definition:** Managers should never be surprised by what enablement is rolling out, because that is something enablement can control.

Chad meets with functional leaders every two weeks, gives them communications to share with their managers, and briefs those managers before a change reaches the field. He says managers then feel like they are in it with enablement.

### Enablement Rituals (11:22)

**Definition:** Standing meetings and communication channels that happen on a known cadence, so reps and managers know why they are showing up and what they will take away.

Chad's examples at Boomi are a monthly enterprise town hall, quarterly training on competitive, product and pricing topics, segment and regional meetings, and consistent Slack, email and newsletter communication. Rituals give enablement places to repeat a message and free reps' attention for customers.

### Umbrella the Ad Hoc Request (14:54)

**Definition:** Slot an ad hoc enablement need into an existing ritual and frame it under a common theme so people see the why and what's in it for them.

Chad says rituals can be re-leveraged for just-in-time learning, and that leaders appreciate it. A product training can be framed as part of increasing ACV this quarter, then measured with conversation intelligence and an outcome such as the share of multi-product deals.

### Written and Taught Sales Process (18:44)

**Definition:** Have a sales process that is both written down and taught, so the team produces more predictable outcomes.

Chad attributes this simple framework to a CRO. With a big team and many new managers it is easy to drift from it, and he tells enablement and ops people to treat that drift as a signal to return to the basics.

### Deal Green Lights (22:06)

**Definition:** The behaviors, outcomes and activity that have to happen at each stage, drawn from the signals that move deals to the next stage the quickest.

Rather than managing to the number of days in a stage, Chad's team codified these green lights into a framework, trained the managers on it, and built it into their calendars and weekly cadence.

### Coach Camps (23:18)

**Definition:** Forums that bring managers together to talk through the management framework in practice and learn from each other.

A former member of Chad's team who now focuses exclusively on managers runs them. Surveys and analysis beforehand keep topics relevant. Seasoned managers share experience and newer managers teach the latest tooling.

### Always-On Coach (24:20)

**Definition:** Agents and alerts in a manager's daily flow that flag the specific coaching opportunity for a rep.

Chad's team is building these into Slack and specific areas of Salesforce, drawing on the agreed process, the framework and particular calls, so the manager sees the one priority to coach to.

### Leading-to-Lagging Metric Link (27:27)

**Definition:** Capture a leading metric enablement can change and correlate it with the revenue outcomes leadership wants.

Chad's example is conversation intelligence mentions rising after training, measured over time and correlated with ACV. He stresses that it is not always causation, and that sharing it incrementally makes investment conversations easier.

### One Point of Conversion (31:00)

**Definition:** Translate enablement into plan math: a small change in yield on the same pipeline has a large revenue effect, in both directions.

Anthony's example is a $20 million bookings plan at 20% conversion on $100 million of pipeline, where one extra point adds $1 million. If new reps drift and conversion falls, the same math works against you.

### Repeat-Question Barometer (38:07)

**Definition:** Measure how often the same or similar questions appear in internal channels, before and after a training.

Chad has measured this in Slack and now uses LLMs to do it. He has seen repeat questions fall and the remaining questions become more deal specific, which he reads as a sign that the foundational training landed.

### Time to Fourth or Fifth Deal (45:40)

**Definition:** Track how long a new rep takes to reach a fourth or fifth deal to see whether they are creating momentum, rather than stopping at time to first deal.

Chad uses it as an early flag for managers. If something wobbles in the first few deals, there is still time to intervene and get the rep on track for the behaviors of a fully productive seller.

### Sales-Process-Oriented Onboarding (47:13)

**Definition:** Build onboarding around the stages of the sales process rather than a sequence of content, so a rep can recall what to do at each point in a deal.

Chad says this speaks the language reps use to think about their work. A rep can recall what to do with an SQL or what resources, behaviors and exit criteria apply when a deal moves to propose, which matters while they are drinking from the fire hose.


## Quotes

_Speakers inferred from an undiarized transcript — verify before attributing._

> "My starting hypothesis was that a more confident seller would be a more effective seller."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (01:31)

> "Sales methodology is super important. But it won't be as effective if we don't do this persona work first."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (02:51)

> "And that co-build is just so critical for enablement."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (06:34)

> "You got to hit them seven ways with seven different messages for things to really sink in."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (08:11)

> "People need to be reminded more than they need to be told or taught."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 149 (09:03)

> "I think one of the things that enablement does have control over is no surprises to the manager group."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (10:55)

> "If folks are interpreting different things about a sales process, you're gonna get different results."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (19:29)

> "It becomes less enablement, less enforcement, and really it becomes empowerment."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (20:57)

> "Every time I've found a way to capture a leading metric to the outcomes, the revenue outcomes that the business or the CRO, CEO wanna drive, I've found success in my career."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (27:34)

> "And lo and behold, we saw our ACV double over that period of time."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (29:36)

> "If you don't change a single other thing, but you improve conversion rate by 1%, you'll add another million dollars of bookings into the plan."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 149 (31:15)

> "If you don't make these investments, the same math works the other way."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 149 (31:37)

> "You have to find a way to get dirty with the data."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (34:20)

> "Nothing gave me more influence, nothing helped me advocate for my team more than having absolute control, conviction and confidence in the data."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 149 (36:11)

> "When you reduce the repeat questions in Slack and email and Jira, wherever, you start to see that the questions become much more deal specific, much more nuanced."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (38:55)

> "We saw our win rate go up 10 points against one competitor and 15 points another."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (42:00)

> "Not looking at time to first deal, but looking at time to fourth or fifth deal."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (45:50)

> "Ramp does not mean they're trained on the product and ready to do a demo."
>
> — Anthony Enrico, The LeanScale Podcast Ep. 149 (46:41)

> "I had a sales leader who said, this is the same thing as like stretching and working out the hammies before you go for a sprint."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (50:46)

> "I think the ones who will succeed are the ones who are leaning into that practice."
>
> — Chad Trabucco, The LeanScale Podcast Ep. 149 (51:17)


## Practical advice by role

### Sales Leaders

- Run a confidence survey at the beginning of each quarter on what was rolled out in the last quarter, and track the change over time.
- Survey managers on their confidence in their teams, and investigate where their scores disagree with the reps'.
- Keep a written and taught sales process, especially when many managers are new to the role.
- Define green lights for each stage from the behaviors that move deals fastest, and build them into a manager's weekly calendar.
- Give managers a peer forum such as a coach camp, with surveys and analysis beforehand so that the topics are relevant.
- Keep repeating fundamentals such as upfront contracts and saving five minutes to close a call with documented next steps.
- Build onboarding around the stages of the sales process, and encourage reps to practice with AI role play before live calls.

### RevOps Leaders

- Help enablement get to data quickly. Chad says he has never worked anywhere that enablement could measure as fast as it wanted.
- Codify methodology behaviors in your conversation intelligence tool, and look back at earlier calls to baseline ad hoc trainings.
- Agree on the definitions of ramp and time to first deal with leadership up front, then add time to fourth or fifth deal as an early signal.
- Track named competitive win rates every quarter, even in a spreadsheet, so a persistent decline can be seen.
- After a training, watch the outcome it was meant to change, such as the percentage of multi-product deals, week over week.
- Accept directional measures, as long as the before and after periods are measured the same way.

### Revenue Executives

- Ask enablement which leading metric it will move and which revenue outcome it should correlate with.
- Translate enablement into plan math by working out what one point of conversion is worth on your own bookings plan.
- Expect enablement to show the impact of the time it takes reps out of the field.
- Before defaulting to more sales training at a kickoff, check whether trend data points to a more specific need.

### Founders

- Do not define ramp as product training and a pitch deck. Look for predictable, reliable output.
- As you add reps quickly, plan for drift, because lower conversion from new reps carries the same math in reverse.
- Invest in manager enablement once a larger team or a cohort of newly promoted top AEs makes the sales process easy to lose.


## AI takeaways

**Thesis:** Chad sees AI changing enablement in three ways: it makes the analysis he once did in spreadsheets far easier, it brings coaching into a manager's daily flow, and it gives reps a place to practice before a live call.

- **** — 
- **** — 
- **** — 
- **** — 
- **** — 
- **** — 
- **** — 

**Agent & automation ideas**

- An always-on coaching agent that reviews calls against stage green lights and tells each manager the one thing to coach a given rep on, in Slack or Salesforce.
- A repeat-question monitor that clusters similar questions in Slack, email and Jira and reports the rate before and after each training.
- A post-training tracker that measures how often trained topics appear in calls and lines that up against ACV or multi-product deal share.
- A pre-call rehearsal agent that builds a role play from the next meeting on a rep's calendar, with the relevant persona and transcripts.
- A ramp monitor that flags new reps whose time to fourth or fifth deal is running behind.


## Operations takeaways

### Revenue operations

- **.** 
- **.** 
- **.** 
- **.** 
- **.** 
- **.** 

### Pipeline & marketing ops

- **.** 
- **.** 
- **.** 
- **.** 
- **.** 


## Metrics mentioned

| Value | Metric | Context |
| --- | --- | --- |
| About 11 years | Chad's time in enablement | He got into enablement by answering RFPs, per the show notes. |
| Roughly $1M to about $60M | Glint ARR growth | Per the show notes, from Chad's start as founding enablement hire to Glint's acquisition by LinkedIn. |
| Four straight years | Win-loss program at Glint | Per the show notes. Win rates were tracked quarter in, quarter out against the top five competitors. |
| About 20% to 60% | AI mentions on calls at Guru | Chad's recollection of the change within two to three months of a series of AI trainings. |
| Doubled | ACV at Guru | Over the same period as the rise in AI mentions. Chad presents this kind of link as correlation, not always causation. |
| 10 and 15 points | Competitive win-rate lift | Against two top competitors in the quarter after a sales kickoff built around peer-to-peer competitive training. |
| Six-figure ACV | Deal size in that win-loss example | Chad's description of the deals affected by the win-rate change. |
| Every two weeks | Leader sync cadence | Chad's standing meeting with functional leaders to keep them ahead of what is happening for their organizations. |
| $1M in bookings | Value of one point of conversion | Anthony's example: a $20 million plan at 20% conversion on $100 million of pipeline. |
| Time to fourth or fifth deal | Early ramp signal | Chad's leading indicator of whether a new rep is creating momentum. |


## Entities mentioned

- **Boomi** (company) — Chad's current employer, where he leads enablement partners embedded in commercial, enterprise, solutions engineering and customer success. Source of his examples of quarterly competitive, product and pricing training, a monthly enterprise town hall, and top performers leaning into AI role play. · https://www.leanscale.team/knowledge/company/boomi/
- **Glint** (company) — Where Chad was the founding enablement hire and first ran the confidence survey. Per the show notes he helped take it from roughly $1M in ARR to about $60M at its acquisition by LinkedIn, and ran its win-loss program for four straight years. The program's competitive win-rate data redirected a sales kickoff. · https://www.leanscale.team/knowledge/company/glint/
- **Guru** (company) — Where Chad built enablement from zero. His survey showed a gap with the HR persona and moved persona training ahead of a new sales methodology, and a series of AI trainings took AI mentions from about 20% to 60% of calls while ACV doubled. Per the show notes, he was such a vocal customer that the team nicknamed him "the Chadvocate" before he joined. · https://www.leanscale.team/knowledge/company/guru/
- **Dixa** (company) — Per the show notes, another company where Chad built enablement from zero. It is not discussed in the conversation. · https://www.leanscale.team/knowledge/company/dixa/
- **Snowflake** (company) — Named with Gong as a place Chad's team looks when triangulating a problem to bring to sales leaders. · https://www.leanscale.team/knowledge/company/snowflake/
- **LeanScale** (company) — Anthony's company, which he started in 2021 after running RevOps at three companies. He closes by noting the conversation will be queryable on LeanScale's MCP. · https://www.leanscale.team/knowledge/company/leanscale/
- **Chad Trabucco** (person, guest) — Director of Enablement Business Partner Strategy and Activation at Boomi; founding enablement hire at Glint. · https://www.leanscale.team/knowledge/guest/chad-trabucco/
- **Anthony Enrico** (person, host) — Co-founder of LeanScale and host of The LeanScale Podcast. · https://www.leanscale.team/knowledge/guest/anthony-enrico/
- **Gong** (tool, Revenue Intelligence) — The conversation intelligence tool Chad names for checking whether trained messages show up on calls and for triangulating problems to raise with leaders. His win-loss spreadsheet at Glint predated it.
- **ChatGPT** (tool, AI Assistant) — Its launch, as Chad tells it, set off the explosion of AI interest that led Guru to make its reps conversant in AI.
- **Slack** (tool, Team Messaging) — Where Chad runs communication rituals, where his team is building coaching alerts for managers, and where he measures repeat questions before and after training.
- **Salesforce** (tool, CRM) — One of the places Chad's team is building alerts that tell managers about opportunities to coach.
- **Jira** (tool, Issue Tracking / Project Management) — Named with Slack and email as a channel where Chad has seen repeat questions fall after training.


## FAQ

**Q: What is a sales rep confidence survey?**

A: A rep confidence survey asks sellers how confident they feel on the topics enablement has covered and tracks the answers over time. Chad Trabucco, who leads enablement partner strategy at Boomi, calls his version the voice of sales and first ran it at Glint. He runs it at the beginning of each quarter, looks back at what was rolled out the previous quarter, and measures whether confidence changed. Because confidence is a leading signal enablement can influence, he can connect it to the quarter's revenue results. He pairs it with win-loss data and runs a parallel survey asking managers how confident they are in their teams.

**Q: What should enablement do when rep and manager confidence scores disagree?**

A: Chad Trabucco of Boomi treats the gap as a discovery opportunity. If reps rate their confidence high and the manager rates the team lower, he probes why the manager sees it that way, understands the pain and builds a program together with that manager. Afterward enablement can show the original pain, how it was solved and what to do next. He says that co-build is critical and turns enablement from enforcement into empowerment.

**Q: How do you prove the ROI of sales enablement?**

A: Chad Trabucco of Boomi ties a leading metric to the revenue outcomes leadership cares about, then shares progress regularly so a budget conversation is not a one-time justification. At Guru, a series of AI trainings took AI mentions from something like 20% of calls to 60% within two to three months, and ACV doubled over that period. He describes these links as correlation, not always causation. At Glint, competitive win rates rose 10 and 15 points against two top competitors the quarter after a sales kickoff focused on them. Host Anthony Enrico adds that on a $20 million plan with 20% conversion, one point of conversion adds $1 million in bookings.

**Q: How should enablement teams support frontline sales managers?**

A: Chad Trabucco of Boomi uses three mechanisms. The first is a documented framework of green lights, the behaviors and outcomes that have to happen at each deal stage, built into a manager's weekly calendar. The second is coach camps, where managers learn from each other on topics informed by surveys and analysis done beforehand. The third is agents and alerts in Slack and Salesforce that flag a specific coaching opportunity for a rep. He says this matters most when teams are scaling quickly and newer managers, often former top AEs, can drift from a written and taught sales process.

**Q: What does "seven times, seven ways" mean in sales enablement?**

A: It is the idea, from a sales leader cited by Boomi's Chad Trabucco, that you have to hit people seven ways with seven different messages before something sinks in. Chad uses it to warn enablement teams against assuming that something trained last quarter is now standard. Fundamentals such as upfront contracts and documenting next steps are what tend to get lost. Regular rituals like quarterly training, town halls, Slack updates and newsletters give enablement the places to repeat a message.

**Q: What metrics should a sales enablement leader track?**

A: Chad Trabucco of Boomi starts with conversation intelligence: whether what reps were taught shows up on calls, with methodology behaviors codified in the tool. He adds repeat questions in Slack, email and Jira, which should fall after training and turn into more deal-specific questions. He also tracks competitive win rates against top competitors, the percentage of multi-product deals after training, rep confidence, time to first deal and time to the fourth or fifth deal. He says an imperfect measure is fine if it is directional and the before and after are measured the same way.

**Q: What does a fully ramped sales rep look like?**

A: A fully ramped rep is not someone who has been trained on the product and can give a demo. Chad Trabucco of Boomi looks for consistent output quarter in and quarter out, then studies the behaviors behind it, such as call activity, self-sourced pipeline, pipeline inspection and requalification. He says leadership must agree on what ramp and time to first deal mean. He also watches time to the fourth or fifth deal as an early sign of momentum, so managers can intervene if something wobbles. Host Anthony Enrico describes ramp as a rep predictably and reliably closing deals and hitting quota.

**Q: How is AI role play used in sales enablement?**

A: AI role-play platforms ingest a company's methodologies and call data so reps, SDRs and customer success teams running QBRs can practice outside live deals. Chad Trabucco of Boomi repeats a sales leader's comparison to stretching before a sprint. Practice lets reps work out the kinks without wasting live pipeline, and he hopes the tools will prepare reps for the specific calls and personas already on their calendars. He says the people leaning into it at Boomi are already the top performers.


## Timeline

- **00:00** — Cold open + intro
- **01:09** — The confidence survey: a leading metric enablement can control
- **05:28** — Surveying managers too, and what to do when the scores disagree
- **16:47** — Why enablement has to invest in managers
- **21:17** — Green lights, coach camps and always-on coaching
- **28:16** — AI mentions from 20% to 60% of calls, and ACV doubled
- **30:48** — One point of conversion = $1M
- **36:00** — The enablement data cockpit
- **48:32** — AI role play: stretching before the sprint
- **52:06** — Wrap


## Related episodes

- **Ep. 112: Why Enablement Fails Before It Starts** (Cheyenne Griffith (Deepgram)) — Another enablement leader on finding leading indicators in how reps talk and making an ROI case, the problem Chad addresses with confidence scores and call mentions.
- **Ep. 135: Where Enablement Goes to Die: The First-Line Manager** (Ally Combs (Bretton AI)) — Makes the case for investing in first-line managers and starting from the conversion funnel, which pairs with Chad's green lights and coach camps.
- **Ep. 60: The Hidden Mistakes of Scaling RevOps and Enablement** (Andy Mowat (Whispered)) — Covers enablement as a neglected function and how managers should use Gong and Chorus for call review, close to Chad's measurement and coaching approach. · https://www.leanscale.team/knowledge/podcast/andy-mowat-scaling-revops-enablement/
- **Ep. 25: The End of Sales Guesswork** (Christina Brady (Luster)) — AI dress rehearsals and a concrete definition of ramp, the two topics Chad finishes on. · https://www.leanscale.team/knowledge/podcast/christina-brady-luster-predicts-gaps/
- **Ep. 45: Turning Sales Teams Into High-Performers with AI** (Yogi Punjabi (PeopleLens)) — Nudging reps inside Salesforce, calendar and Slack and measuring methodology adoption from conversations, alongside Chad's always-on coaching alerts. · https://www.leanscale.team/knowledge/podcast/yogi-punjabi-high-performers-ai/
- **Ep. 142: How to Sell Against Claude: Differentiation Is a System** (Simon Kirk (Orbital)) — Argues that frontline managers must reinforce training or it dies after one session, and Anthony runs the same one-point-of-conversion math on a $20 million plan.


## Full transcript

_Machine-transcribed and not diarized; speaker attribution is inferred._  
_Transcript only, as a separate file: https://www.leanscale.team/knowledge/podcast/chad-trabucco-boomi-confidence-is-a-metric/transcript.md_

### 00:00 — Cold open + intro

**[0:00]** And when you come at it from that framework,

**[0:02]** and you really are co-building with the managers,

**[0:04]** that's where it's just so fun to enable.

**[0:06]** My guest today is Chad Trebucco, who

**[0:09]** leads enablement, business partner strategy,

**[0:11]** and activation at UMI.

**[0:12]** My starting hypothesis was that a more confident seller

**[0:16]** would be a more effective seller.

**[0:18]** And confidence also gave me an enablement,

**[0:20]** sort of this leading signal, this leading measure,

**[0:24]** that I could influence and control.

**[0:26]** Nothing gave me more influence.

**[0:28]** Nothing helped me advocate for my team

**[0:30]** more than having absolute control, conviction,

**[0:33]** and confidence in the data.

**[0:37]** It was 60% of the calls they were talking about AI.

**[0:41]** But look at this change.

**[0:42]** We've changed this behavior significantly.

**[0:45]** Let's take a look at our ACV.

**[0:47]** And lo and behold, we saw our ACV double over that period.

**[0:50]** I've never done a presentation or walked into a big meeting

**[0:55]** without doing a dry run.

**[0:56]** I think the ones who will succeed are the ones who

**[0:58]** are leaning into that practice.

**[1:00]** And we're already seeing it here.

### 01:09 — The confidence survey: a leading metric enablement can control

**[1:09]** Chad, you've been running a quarterly survey that

**[1:11]** asks reps how confident they feel competitively on product,

**[1:16]** on moving up market.

**[1:17]** Take me back to the first time you ran that survey.

**[1:21]** And what did the answers tell you

**[1:23]** that you didn't already know?

**[1:26]** Yeah, it's a great question.

**[1:28]** So at Glint, this is where we started to run this.

**[1:31]** My starting hypothesis was that a more confident seller would

**[1:35]** be a more effective seller.

**[1:36]** And confidence also gave me an enablement,

**[1:39]** sort of this leading signal, this leading measure,

**[1:43]** that I could influence and control,

**[1:45]** and then connect it to the quarter's revenue results.

**[1:49]** So asking about it regularly over time,

**[1:52]** through this mechanism that I called the voice of sales,

**[1:57]** really gave me a direct view into where sellers needed help.

**[2:01]** And the clearest example of a survey changing

**[2:04]** sort of a decision that came later, sort of an aha for me,

**[2:08]** was when I was at Guru.

**[2:10]** Initially, leadership was prepared to bring in

**[2:13]** a new sales methodology.

**[2:15]** And that was in the discussions before I even started there.

**[2:19]** And when I landed there, I ran this survey,

**[2:23]** brought that idea over to Guru, ran this survey

**[2:25]** within my first couple of weeks.

**[2:28]** And it showed a really immediate gap with the field

**[2:30]** in speaking to one of the core personas, this HR persona,

**[2:35]** which was really core to going larger in accounts

**[2:38]** and selling the full stack across the full company.

**[2:43]** And so that was a critical point for the field.

**[2:45]** And it gave me this lens to come back to leadership and say,

**[2:51]** hey, sales methodology is super important.

**[2:53]** But it won't be as effective if we don't do this persona work

**[2:59]** first.

**[3:01]** And so we did that persona training first.

**[3:03]** I scored the reps on how they played both the seller,

**[3:07]** sort of did this role play.

**[3:09]** But also, I scored them on how they played the buyer

**[3:11]** so that they really engendered sort of the motivations

**[3:14]** of the buyer and started to think like that persona.

**[3:18]** So this really changed our priorities in sort of the cadence

**[3:21]** that we were rolling out.

**[3:22]** And it built trust with the sellers

**[3:25]** so they could see that I was in there--

**[3:28]** I was looking after their impact.

**[3:33]** And I can impact that story a little bit more.

**[3:35]** But that's really where I got started

**[3:37]** in this idea of confidence.

**[3:41]** I think it's unbelievably unique.

**[3:43]** I haven't met an enablement leader

**[3:45]** that has been running it that way.

**[3:47]** But it makes a ton of sense.

**[3:50]** It feels like it unlocks a whole realm of information

**[3:53]** that you wouldn't otherwise have access to

**[3:55]** and really gives you the way to lean in.

**[3:58]** How often are you running the survey?

**[4:00]** Do you kind of cohort it?

**[4:02]** Do you have different surveys for different go-to-market teams?

**[4:04]** Operationally, what does it look like and how do you run it?

**[4:08]** Yeah, operationally, I think I haven't

**[4:11]** run it for different groups.

**[4:14]** It was sort of more general.

**[4:16]** And I think that was by design to really capture--

**[4:21]** I could clean it up on the back end

**[4:22]** and see the titles and different things

**[4:24]** and sort of condense it there.

**[4:26]** When I was running it, the teams were smaller.

**[4:28]** So I really didn't need to specify it.

**[4:31]** But the mechanism was looking back

**[4:34]** at the last quarter of things we rolled out,

**[4:35]** measuring the confidence on the things that we did,

**[4:38]** and then seeing if there's a delta going forward.

**[4:40]** And I think data is so important when you have the trend.

**[4:43]** And so running this quarter in, quarter out,

**[4:45]** beginning of the quarter, minds are fresh,

**[4:48]** sort of take a chance to look back,

**[4:50]** I think was a really critical way to show progress over time.

**[4:55]** And I think that helped me understand,

**[4:58]** are we moving the needle in these certain areas?

**[5:01]** What do I need to surface to leadership?

**[5:03]** We can get a little bit more into the win-loss program

**[5:07]** that we ran.

**[5:08]** But coupling that with this voice of sales

**[5:10]** really gave us sort of the business view, the company

**[5:13]** view, that win-loss level.

**[5:15]** We married that with sort of the voice of the field.

**[5:17]** And that can help us triangulate a lot in terms of the way

**[5:21]** that we bring enablement programs to market

**[5:23]** and really focus on sort of a data-driven approach.

### 05:28 — Surveying managers too, and what to do when the scores disagree

**[5:28]** Are you measuring also at the management level of the team?

**[5:32]** Or is this more of like a field-level survey

**[5:34]** that you're running?

**[5:36]** Yeah, I would also run a confidence survey

**[5:38]** with the managers.

**[5:39]** And that wasn't like, are you confident being a manager?

**[5:42]** I think it was, are you confident in your team's ability

**[5:46]** to do these different things?

**[5:48]** And that gave me just like another way

**[5:50]** to triangulate how the team is approaching things.

**[5:54]** And when those things disagreed,

**[5:56]** I think it was really interesting to probe into that

**[5:59]** and see, hey, the rep's confidence is really high.

**[6:02]** Some ways you want a really confident rep.

**[6:05]** The manager's confidence in that rep or that team

**[6:08]** was a bit lower.

**[6:09]** And so that gave me an opportunity

**[6:11]** to kind of do what we're telling all of our sellers to do.

**[6:13]** And that's do a little more discovery,

**[6:15]** probe a little bit deeper, understand the pain,

**[6:18]** and then tie that to the value

**[6:21]** that we can drive on the backend

**[6:22]** if we really understand what the manager is trying to get at.

**[6:25]** Why do they see that as a lower score

**[6:28]** or lower confidence in that team?

**[6:31]** And then you build a program around that with them.

**[6:34]** And that co-build is just so critical for enablement.

**[6:37]** It really drives things forward.

**[6:38]** And then you can show on the backend,

**[6:40]** hey, we proved this point.

**[6:41]** Here was your pain.

**[6:42]** Here's how we solved it.

**[6:43]** What can we do next?

**[6:47]** - Are there any common insights?

**[6:51]** I'm sure this will depend on the company

**[6:53]** and the market they're competing in

**[6:55]** and all different types of things.

**[6:57]** But since you've been running this for a while,

**[7:01]** are there a few common things that tend to come up

**[7:04]** where people don't feel as confident

**[7:06]** as maybe people would assume that they'd be confident in?

**[7:10]** Is it product knowledge?

**[7:12]** Is it competitive information?

**[7:14]** Is it market knowledge?

**[7:16]** Anything that tends to come up quite often.

**[7:18]** - I really haven't found a common trend

**[7:20]** across companies from the survey data.

**[7:23]** I think it depends on the situation.

**[7:26]** Rep's heads are down.

**[7:27]** They've got a big quarter generally coming up.

**[7:30]** I do find surprises though.

**[7:32]** And I think there are some surprises

**[7:34]** and I think this is more of a gut feel

**[7:36]** and sort of a thematic theme that I've seen

**[7:41]** across companies and that's the fundamentals.

**[7:43]** I think reps realize some of the fundamentals get lost

**[7:48]** in all of the things that we're doing,

**[7:51]** all of the things that we're pushing.

**[7:53]** I think enablement can get lost in,

**[7:55]** well, we trained on that last quarter

**[7:57]** so it should be sort of like standard

**[7:59]** for folks this quarter.

**[8:01]** And that's not always the case.

**[8:02]** I think folks need time to catch up.

**[8:04]** I think folks need time to absorb.

**[8:08]** I have the sales leader that always says it's seven times seven.

**[8:11]** You got to hit them seven ways

**[8:12]** with seven different messages

**[8:15]** for things to really sink in.

**[8:16]** And I think that realization is really true.

**[8:20]** And sometimes that extends to the fundamentals

**[8:23]** of like, are you doing an upfront contract?

**[8:25]** Are you creating five minutes to close the call

**[8:28]** and make sure that you've got your next steps documented

**[8:31]** with the prospect and coming back to those things

**[8:34]** and reminding the team that those fundamentals are important

**[8:38]** and they're reminding them why

**[8:40]** in all of the things that they're doing.

**[8:42]** So it's not necessarily a realization from the data.

**[8:48]** It's more of a gut feel

**[8:49]** and a trend that I've seen across companies.

**[8:51]** - Yeah, and I'm assuming,

**[8:53]** I think some people may think,

**[8:55]** okay, you're all at the enablement program,

**[8:57]** you did the training and now you're all done, great job.

**[9:00]** Well, it's just like anything else,

**[9:02]** maybe like diet and exercise.

**[9:03]** People need to be reminded

**[9:06]** more than they need to be told or taught.

**[9:09]** And also if you're working in a scaling company,

**[9:11]** you're continually adding in new reps

**[9:13]** and cycling and cycling people out, cycling people in.

**[9:16]** And some of the things,

**[9:18]** even though it may sound like you're a broken record

**[9:20]** at a certain point,

**[9:21]** but like you need to keep reminding them

**[9:23]** of those fundamentals.

**[9:24]** So that way when they're in the field,

**[9:27]** it's not that they've just been taught about it,

**[9:29]** but it becomes the muscle memory they use

**[9:31]** in the sales process.

**[9:33]** Are there certain cadences you like to follow

**[9:37]** for training and reminding?

**[9:40]** How do you, 'cause this is a very, very tough job

**[9:43]** to keep the ball moving and all this stuff.

**[9:46]** Is there any schedule that you like to follow

**[9:49]** to keep all this top of mind with the reps?

**[9:54]** - Yeah, I think one thing I've learned lately,

**[9:57]** and I think we can kind of probe into this a bit more

**[9:59]** when it comes to the managers.

**[10:01]** But I think it's really important

**[10:03]** to think about the hierarchy

**[10:05]** in the way that you communicate.

**[10:07]** And I think generally we're all moving so quickly.

**[10:12]** We're building agents, we're rolling things out,

**[10:15]** we're pushing things out,

**[10:16]** enablements sort of on the bleeding edge

**[10:18]** of everything new and moving forward.

**[10:21]** Sometimes we forget that hierarchy of communication

**[10:24]** is really important.

**[10:25]** So I have a standing meeting with all my leaders

**[10:29]** across all of those different roles.

**[10:31]** So the heads of, the VPs of,

**[10:35]** the global heads of every two weeks

**[10:38]** so that I can keep them abreast

**[10:39]** of the things that are happening for their org.

**[10:42]** And then when a new thing is happening,

**[10:44]** we're sort of like getting in front of it,

**[10:46]** giving them comms to share with their managers,

**[10:48]** and then we're proactively sharing

**[10:50]** with their managers as well before those things happen

**[10:53]** so that there's no surprises.

**[10:55]** I think one of the things

**[10:55]** that enablement does have control over

**[10:58]** is no surprises to the manager group.

**[11:01]** And so I'm really pushing that with my team

**[11:03]** and they're working closely with their managers

**[11:06]** because managers have one of the tougher jobs

**[11:08]** in addition to reps.

**[11:10]** And when you create that mantra of no surprises,

**[11:14]** they really do feel like they're in it with you.

**[11:16]** And then you communicate to the field

**[11:19]** that these things are happening,

**[11:20]** this training is happening.

**[11:22]** I also think it's really important to have rituals.

**[11:25]** And when I say rituals,

**[11:27]** I mean a constant team meeting

**[11:30]** that happens every quarter or every month

**[11:34]** within sort of the larger business.

**[11:37]** So we have an enterprise town hall that happens every month.

**[11:41]** That's an important ritual for enablement

**[11:43]** to know about and lean into.

**[11:45]** Then I think there's important rituals

**[11:46]** from a learning perspective.

**[11:47]** And we have this really cool model here at Boomi

**[11:50]** where we do something quarterly.

**[11:51]** There's quarterly training that includes

**[11:54]** the most important things, right?

**[11:55]** Competitive training, product training, pricing training.

**[11:59]** And that is a ritual that reps know

**[12:01]** is gonna happen every quarter, quarter in, quarter out.

**[12:04]** And then there's a sort of a cadence

**[12:06]** and a calendar below that

**[12:09]** that enablement can plug into.

**[12:11]** We spotlight what's great

**[12:13]** and we have these vehicles or these rituals

**[12:16]** at sort of every segment, every region

**[12:20]** that we can plug into that the reps know,

**[12:22]** the managers know what happens during that ritual,

**[12:26]** what to expect.

**[12:27]** And again, that comes back

**[12:28]** to that sort of no surprises mantra.

**[12:31]** I think that just keeps them focused

**[12:33]** on what they need to do

**[12:34]** when these things pop up on the calendar.

**[12:36]** They know why they're being asked to show up.

**[12:38]** They know what they're gonna get.

**[12:39]** They know what they're gonna take away.

**[12:41]** And then there's rituals beyond that, right?

**[12:43]** There's communication rituals in Slack or email.

**[12:46]** And if you keep those consistent,

**[12:48]** you keep a newsletter going of

**[12:50]** these are the things we taught you.

**[12:51]** These are the resources you have.

**[12:54]** Those rituals really become part of the behavior.

**[12:57]** And I think, you know, it does a couple of things.

**[12:59]** For enablement gives you a lot of places

**[13:01]** to sort of hit that seven times, seven ways.

**[13:05]** But it also for the reps, you know,

**[13:08]** takes the mind's share out of sort of what's happening.

**[13:11]** What is enablement doing?

**[13:12]** What is enablement asking me?

**[13:14]** They sort of know when and where that will happen.

**[13:17]** So they can keep more mindshare on what they do day in,

**[13:20]** day out.

**[13:21]** And that's working with the customers and prospects.

**[13:24]** - I think those sacred rituals are super important

**[13:28]** and giving people, you know, an expectation

**[13:31]** of when they'll be given information,

**[13:33]** which sounds like a really important work stream.

**[13:36]** Are there ad hoc work streams

**[13:38]** that tend to come up in enablement too?

**[13:40]** Maybe more of like a signal based,

**[13:42]** hey, this thing happens.

**[13:43]** So now enablement has to come in and intervene or help.

**[13:47]** Are there any things like that that come up

**[13:49]** and what's giving you the ability to see opportunities

**[13:52]** to lean in and help with the team?

**[13:54]** - Yeah, I mean, it comes back to the data.

**[13:56]** And I think those ad hoc moments are really critical, right?

**[13:59]** A leader will sort of say in those bi-weeklys that I have,

**[14:02]** hey, this is something I'm seeing.

**[14:04]** Enablement's bringing something forward.

**[14:06]** Hey, we were analyzing GONG.

**[14:07]** We were looking at Snowflake.

**[14:09]** We triangulated this problem.

**[14:11]** You know, is this a problem you're seeing?

**[14:13]** How do we address it?

**[14:14]** And I think that's sort of where the fun

**[14:17]** and the art of enablement can come through of like,

**[14:21]** okay, we have all these things on the plate,

**[14:23]** but we need to do this other thing.

**[14:24]** And I think that's where those rituals

**[14:26]** actually become really important.

**[14:28]** 'Cause you can modulate those rituals.

**[14:29]** It doesn't always have to be,

**[14:31]** this product training is always on X.

**[14:33]** Or this window of time is always on product

**[14:36]** or always on competitive.

**[14:38]** And you can re-leverage those windows.

**[14:41]** And I think leaders actually really appreciate

**[14:44]** when you can re-leverage those windows for those ad hoc things

**[14:48]** and plug in sort of just-in-time learning.

**[14:52]** And I always try to tell my team like,

**[14:54]** let's umbrella this, you know, around a common theme.

**[14:59]** So if we're doing product training

**[15:02]** and there's sort of like this ritual of,

**[15:03]** hey, we're gonna level you up around this product training,

**[15:07]** but we get one of those ad hoc requests of like,

**[15:10]** hey, this is a thing we need to lean into.

**[15:13]** You can sort of say, hey, well, this is part of us,

**[15:17]** you know, increasing ACV this quarter

**[15:19]** if you focus on this product training.

**[15:21]** And so you just sort of umbrella these things

**[15:23]** for the reps, the managers as to the why

**[15:27]** and how it fits into the larger context.

**[15:29]** So those ad hoc programs can feel like

**[15:32]** they were part of something larger

**[15:34]** and there's a what's in it for them.

**[15:37]** I think that's always a critical way to connect the dots.

**[15:41]** And then I think the other piece around this ad hoc stuff

**[15:45]** is how are you measuring it?

**[15:47]** How are you sort of showing, you know,

**[15:50]** we're doing this training.

**[15:51]** Here's sort of the way that we're gonna be watching it,

**[15:54]** Gong or other conversational tools.

**[15:57]** And then here's the outcome that we're hoping to drive.

**[15:59]** I talked a little bit about ACV.

**[16:01]** We're hoping to increase ACV by selling more products

**[16:04]** or, you know, more than one product for this initiative

**[16:10]** or this ad hoc request.

**[16:13]** So we're gonna be looking at multi-skew

**[16:15]** and we're gonna see, does that ACV

**[16:16]** or does the percentage of multi-skew deals

**[16:20]** go up over time post-training?

**[16:24]** I think it's really important to measure that

**[16:26]** week over week and then you bring it back to those rituals

**[16:28]** of the syncs with the leaders and the managers.

**[16:31]** So you can show like, hey, we really are in this with you.

**[16:34]** We're looking at it in the same ways

**[16:35]** that you're looking at it.

**[16:37]** And that North Star number that we're all trying to change,

**[16:41]** because of that request,

**[16:42]** something that we're all looking at and working towards.

### 16:47 — Why enablement has to invest in managers

**[16:47]** - One thing that I'm hearing that is really unique.

**[16:51]** I haven't heard a lot of enablement leaders

**[16:54]** spend the amount of focus that you have spent

**[16:57]** on the managers and management layer of the team.

**[17:02]** I think there's a lot of attention that goes on people

**[17:05]** in the field and the reps and individual contributors,

**[17:08]** giving them trained up, monitoring how they're doing.

**[17:10]** But I'm hearing a lot of attention to that management layer.

**[17:14]** Do you have a philosophy around where and when

**[17:17]** and how to invest your time?

**[17:20]** - Yeah, I think what I've learned

**[17:22]** and I was fortunate early in my career,

**[17:25]** particularly at Glint, we had some very seasoned managers

**[17:29]** that didn't need a whole lot of enablement per se.

**[17:33]** They needed visibility.

**[17:34]** And I think that's sort of where the trends were going.

**[17:37]** I think that's why that win-loss program

**[17:38]** was really critical 'cause it gave them

**[17:41]** sort of that company lens and then they were able to see

**[17:44]** how their team was feeling from that voice of sales

**[17:47]** and sort of understand where their team needed support.

**[17:51]** And then they were seasoned enough to be able to lean in

**[17:54]** in those different ways and work with me to do that.

**[17:57]** But I think as I'm realizing, as we move

**[18:00]** sort of into this AI world and teams are scaling

**[18:04]** really, really quickly, I think it becomes

**[18:08]** even more important with these newer managers

**[18:11]** to really enable them on the behaviors that we wanna see.

**[18:16]** And it's creating sort of this foundational layer

**[18:19]** of expectation of how you run your business.

**[18:23]** I think when you have a cohort of newer managers

**[18:28]** that maybe were top AEs that have moved into that role

**[18:32]** or you have a much bigger org, frankly,

**[18:35]** I think that's to your point,

**[18:37]** when do you start to look at managers

**[18:39]** as an area to enable to?

**[18:44]** I think it's that because I have this CRO talk about

**[18:47]** just like a very simple framework.

**[18:51]** We have a written and we have a taught sales process.

**[18:56]** And when the team knows that,

**[18:58]** they'll be much more predictable

**[19:00]** in terms of the outcome that they're driving.

**[19:03]** And I keep coming back to that.

**[19:04]** It's something I think about a lot.

**[19:06]** And when you have a big team,

**[19:08]** you have a lot of new managers,

**[19:10]** it can be very easy to get away from sort of that written

**[19:13]** and taught sales process.

**[19:15]** And so I think that's something to look out for a signal

**[19:19]** for any enablement person or even ops person out there

**[19:23]** is when you see that happening,

**[19:27]** it's really important to come back to the basics

**[19:29]** because if folks are interpreting different things

**[19:33]** about a sales process, you're gonna get different results.

**[19:36]** And I think that predictability is so important,

**[19:39]** particularly in the speed that we're all moving.

**[19:43]** So that would be sort of the way

**[19:45]** that I think about enabling the managers.

**[19:48]** And we can talk a bit more about what does that look like?

**[19:50]** How are we doing that?

**[19:51]** Why is that an aha for me?

**[19:54]** - Yeah, well, and I think a lot of it too

**[19:56]** comes down to reinforcement.

**[19:58]** It's one thing to teach the process,

**[20:00]** put it on paper, like you mentioned,

**[20:02]** and teaching is more than a single session.

**[20:06]** I have young kids, I could tell them to do something,

**[20:08]** but usually it requires a little bit of reinforcement,

**[20:11]** not saying sales reps are children,

**[20:12]** but there's some commonalities between the two.

**[20:17]** And I think if you do a really, really good job

**[20:19]** of enabling the managers,

**[20:22]** then they can help with the day-to-day reinforcement

**[20:24]** when they're coaching their reps,

**[20:26]** when they're digging deep into a deal,

**[20:28]** making sure that, hey, yeah, we're following the process

**[20:30]** that we all agreed on, gives us the best chance of winning,

**[20:35]** then that investment can compound throughout the whole team,

**[20:38]** especially as you're scaling.

**[20:40]** - Your point is so well taken that, hey,

**[20:42]** we've agreed upon this because this is the best way

**[20:46]** for us to accelerate deals, close deals.

**[20:50]** And when you come at it from that framework

**[20:52]** and you really are co-building with the managers,

**[20:54]** that's where it's just so fun to enable

**[20:57]** because it becomes less enablement, less enforcement,

**[21:01]** and really it becomes empowerment.

**[21:02]** And I think that's a framing

**[21:04]** that I really like to anchor into is like,

**[21:07]** how can we empower these managers?

**[21:09]** How can we empower these reps to carry

**[21:12]** what great looks like forward?

**[21:14]** I mean, I think that's the game that we're in.

### 21:17 — Green lights, coach camps and always-on coaching

**[21:17]** - Specifically, what cadence do you set up

**[21:19]** with the managers and how do you like to enable them?

**[21:22]** Are you helping them come up with the methodologies?

**[21:25]** Are you getting things on paper for them?

**[21:27]** Are you producing materials for their team?

**[21:29]** Are you surfacing the insights through transcripts

**[21:33]** or the confidence survey?

**[21:36]** What are all the ways where like tactically,

**[21:39]** okay, this is how I prepare a manager

**[21:41]** to help manage their teams

**[21:43]** from an enablement perspective?

**[21:45]** - Yeah, it's all of those, right?

**[21:48]** It's the written process, right?

**[21:51]** If you can't measure it, you can't document it,

**[21:54]** and it's not gonna be as important,

**[21:55]** and it's not gonna be consistent.

**[21:56]** And so we've done a lot of work

**[21:59]** to take the signals that we see in our data

**[22:02]** that move deals from one stage to the next, the quickest.

**[22:06]** What are those, we call them the green lights.

**[22:09]** What are those green lights that happen at every stage?

**[22:12]** What are the things that have to happen?

**[22:13]** What are the behaviors, the outcomes, the activity?

**[22:18]** 'Cause it isn't always the sort of,

**[22:20]** oh, well, this stage takes 20 days,

**[22:22]** this stage takes 40 days, let's measure that.

**[22:25]** It's really the behaviors that underlie that,

**[22:27]** the things that are happening that drive that

**[22:29]** that are so important.

**[22:31]** So we've sort of codified those green lights

**[22:34]** into this framework

**[22:35]** that we're then training all of the managers on,

**[22:38]** it's documented, and it's built into their rhythm.

**[22:40]** It's built into their calendar, their cadence

**[22:43]** of what their week, what their day looks like.

**[22:47]** And I think we've had a lot of success sort of spelling out,

**[22:52]** these are the things that you should be doing

**[22:53]** and looking at in a week in, week out,

**[22:57]** in almost a calendar format.

**[22:58]** So we're sort of building in that framework

**[23:01]** of this is what our process looks like,

**[23:03]** and this is what your process should look like as a manager.

**[23:06]** And then we're creating these sort of rituals.

**[23:09]** I have a person that I work closely with

**[23:12]** who's running this, used to be on my team,

**[23:14]** has been elevated into this role

**[23:16]** to focus exclusively on managers.

**[23:18]** And he calls these things coach camps.

**[23:21]** And it's a really interesting ritual

**[23:23]** to bring the managers together

**[23:25]** to talk through that ritual, that framework.

**[23:30]** What is it looking like in practice?

**[23:31]** And there's some surveys that go on prior,

**[23:34]** there's some analysis that go on prior

**[23:35]** so that the topics are really relevant

**[23:38]** and they have an opportunity to talk through as a team.

**[23:41]** And I think that peer-to-peer learning can be so critical

**[23:45]** both at the rep level, but also at the manager level.

**[23:48]** And this gives them sort of that forum

**[23:52]** to learn from one another, some of the newer managers,

**[23:56]** to learn from those who are more seasoned.

**[23:58]** Some of the newer ones might be more apt

**[23:59]** to understand the latest tooling.

**[24:01]** And so they're teaching those who've been there longer

**[24:05]** and have more of a standard way that they go about things.

**[24:09]** And so it becomes this wonderful cross-pollination.

**[24:13]** So there's sort of the documentation,

**[24:16]** there's the peer-to-peer learning

**[24:18]** and sort of those focused time.

**[24:20]** And then sort of the third thing that I think

**[24:22]** is really critical, especially now

**[24:24]** with all of the tooling that we have from an AI perspective

**[24:28]** is we're building agents, we're building alerts

**[24:32]** into that daily flow, into Slack,

**[24:36]** into specific areas within Salesforce

**[24:40]** that are alerting the managers

**[24:41]** on those opportunities to coach.

**[24:43]** And I think we haven't talked too much about coaching,

**[24:45]** but that's what managers can be good at.

**[24:49]** Most of them have sat and seen.

**[24:51]** Most of them have seen a lot more opportunities

**[24:55]** than their reports.

**[24:57]** And I think creating some signal in all of the noise

**[25:00]** of these are the two things you can do.

**[25:03]** This is the one priority that you want to coach to

**[25:07]** for this particular rep based on these things

**[25:10]** that have happened, based on the framework

**[25:12]** that we've established, based on the process

**[25:15]** that we've established, based on this call or that call,

**[25:19]** and kind of pulling all those things together, right?

**[25:22]** The framework, the peer-to-peer learning

**[25:26]** and sort of like that condensed time

**[25:27]** to sort of learn and explore.

**[25:29]** And then this kind of always on coach,

**[25:32]** that's something we're leaning into a lot more

**[25:34]** sort of exploring now.

**[25:36]** And I think there's a lot of opportunity with AI

**[25:39]** to make that happen in ways

**[25:42]** that we haven't been able to do before.

**[25:46]** - I love that.

**[25:47]** I think the one that sticks out to me the most

**[25:49]** is the coach camps and getting managers, coaching themselves.

**[25:53]** Again, we think a lot about how enablement is for the reps,

**[25:57]** for the people on the front lines.

**[25:59]** And I think the managers get left out of this quite often.

**[26:02]** And by the way, often you're getting managers

**[26:04]** that were just a rep a couple of days ago,

**[26:06]** and now they're put in this position

**[26:07]** to go lead all these teams.

**[26:09]** And it's new for them too.

**[26:11]** There's a new job that needs to be done,

**[26:13]** ways in which you can manage best practices they can follow.

**[26:16]** And then all of the insights

**[26:17]** that you can help give them ideas like,

**[26:18]** hey, did you know you could coach your rep

**[26:21]** over here on this thing that should help them

**[26:23]** and nudging them in the right direction?

**[26:24]** I mean, it's unbelievably helpful.

**[26:28]** One thing I think a lot of enablement teams struggle with,

**[26:34]** and I'd love your insights and feedback on this,

**[26:37]** is how to articulate the value of enablement.

**[26:42]** And oftentimes when you're wanting to add headcount,

**[26:47]** expand the team,

**[26:49]** it's under a lot of scrutiny from the CFO, the CEO.

**[26:54]** I think sometimes the CRO intuitively understands

**[26:56]** where the investment is,

**[26:57]** but how are you articulating that value

**[27:01]** to advocate for more investment and enablement

**[27:04]** as the company grows and scales?

**[27:06]** - Yep.

**[27:07]** I mean, it's the best when a CRO intuitively gets that.

**[27:10]** I think those are the next areas to work.

**[27:12]** - Sometimes they need help backing it up too.

**[27:14]** Like you gotta work then with the business case with the CFO.

**[27:17]** - Totally, totally.

**[27:18]** Yeah, like you said, it's sort of a gut level,

**[27:21]** but when you can speak their language,

**[27:22]** I think that's when it makes it the most fun

**[27:24]** and it just becomes a no-brainer.

**[27:27]** I really, I come back to this idea

**[27:30]** of leading and lagging metrics.

**[27:32]** And every time I've been able to do this,

**[27:34]** every time I've found a way to capture a leading metric

**[27:40]** to the outcomes, the revenue outcomes

**[27:42]** that the business or the CRO, CEO wanna drive,

**[27:46]** I've found success in my career.

**[27:48]** And those leading metrics can be something as simple as,

**[27:52]** are we seeing gone mentions,

**[27:54]** conversational intelligence mentions go up post-training,

**[27:59]** measuring that over time

**[28:01]** and seeing sort of the behavior change

**[28:04]** that enablement caused and then correlating it.

**[28:08]** It's not always causation,

**[28:09]** but correlating it, by the way, we saw this thing change,

**[28:13]** we saw this increase.

### 28:16 — AI mentions from 20% to 60% of calls, and ACV doubled

**[28:16]** When I was a guru, it was right at the cusp

**[28:19]** of chat GPT coming out and there was this explosion

**[28:23]** of like AI this, AI that, what does it mean?

**[28:26]** And we really needed to make our team conversant

**[28:28]** in AI language.

**[28:29]** There was always, there had already been AI built

**[28:33]** into the system, but we needed to make the team

**[28:35]** more conversant in what is AI for guru?

**[28:40]** How are we thinking about it?

**[28:41]** What are we doing?

**[28:42]** And so we ran this training series of trainings

**[28:46]** to kind of like bring them up to speed on,

**[28:49]** what's the latest?

**[28:51]** What is the product level capabilities with regards to AI?

**[28:55]** We want you to be proactively talking about this more.

**[28:59]** So we measured that and we measured it.

**[29:01]** I think it was something like 20% of the calls

**[29:04]** that they were having at the time,

**[29:07]** that was sort of our baseline included AI,

**[29:10]** some measure of AI in there.

**[29:13]** And after this training, we saw it go up

**[29:15]** and we actually saw it go up.

**[29:17]** It's such a steep curve within two to three months

**[29:20]** that it was 60% of the calls they were talking about AI.

**[29:25]** So I was able to sort of come back and say,

**[29:27]** well, look at this change.

**[29:28]** We've changed this behavior significantly.

**[29:30]** Let's take a look at our ACV.

**[29:33]** Let's take a look at how our deals are progressing.

**[29:36]** And lo and behold, we saw our ACV double

**[29:38]** over that period of time.

**[29:40]** So it's conversations like those that make a real difference

**[29:44]** to building that investment,

**[29:46]** to building more headcount, to articulating.

**[29:50]** If we can do this, imagine what we can do over here.

**[29:54]** And I think it comes back to that reporting, right?

**[29:56]** Like those rituals.

**[29:58]** If you're constantly sort of sharing,

**[30:00]** hey, this is incrementally how we've changed things.

**[30:03]** This is how it rolls up to the top line number

**[30:05]** that you're the North star that you're most concerned about.

**[30:08]** If you're constantly doing that,

**[30:10]** it doesn't become this like big ask

**[30:13]** and there's not this like,

**[30:15]** I've got to present this business justification.

**[30:17]** You may have to, it depends on the company,

**[30:19]** but it becomes a lot easier if incrementally over time,

**[30:23]** you've constantly been sharing,

**[30:24]** hey, we've added this many QOs

**[30:27]** based on this training that we've done

**[30:29]** or in correlation with this training that we've done.

**[30:32]** And it's showing up in sort of the bottom line number

**[30:36]** of the deals that we're now closing.

**[30:38]** When you can do that over time,

**[30:41]** it makes those conversations much easier,

**[30:44]** much more streamlined

**[30:45]** and kind of a no-brainer for everybody.

### 30:48 — One point of conversion = $1M

**[30:48]** - I also don't think some people understand the magnitude

**[30:51]** of what increasing conversion rate

**[30:54]** or increasing ACV can do and what it can be.

**[30:58]** I'll give an easy example.

**[31:00]** If you're on a $20 million booking plan

**[31:03]** and let's say you have a 20% conversion rate,

**[31:06]** so you need $100 million to build a pipeline to get there.

**[31:11]** On the same pipeline with the same reps,

**[31:13]** with the same pricing, with the same everything,

**[31:15]** if you don't change a single other thing,

**[31:17]** but you improve conversion rate by 1%,

**[31:20]** you'll add another million dollars of bookings

**[31:22]** into the plan.

**[31:24]** - Yeah.

**[31:25]** - One small minor improvement can pay for enablement

**[31:32]** over and over again.

**[31:34]** And by the way, that's the opportunistic approach to it.

**[31:37]** If you don't make these investments,

**[31:40]** the same math works the other way.

**[31:42]** - Yeah.

**[31:43]** - If you start to experience drift with your new reps

**[31:47]** not performing as well as what the experienced reps are

**[31:50]** and that conversion rate starts to dip down,

**[31:52]** you could be losing millions of dollars as well.

**[31:55]** So I think the teams that can articulate

**[31:58]** the numbers really well,

**[31:59]** I know it's not always fun selling yourself

**[32:01]** and constantly advocating for what you're doing.

**[32:06]** And you don't have to take whole credit for it,

**[32:08]** but you do have to say like,

**[32:11]** I don't know the exact number that's attributed

**[32:13]** to everything I did,

**[32:14]** but I do know we influenced it and it's correlated.

**[32:17]** And there's immense value in keeping the yield

**[32:21]** as high as possible with your team.

**[32:24]** I also think there's an interesting note in there of like,

**[32:29]** you're also taking reps off the field

**[32:32]** or out of the field to do enablement.

**[32:35]** And so I think there's like an implicit justification too

**[32:39]** and enablement has the responsibility to say,

**[32:42]** here's the impact of that time investment

**[32:45]** that I'm requiring from your team, from your managers.

**[32:49]** I think it also goes to that point too.

**[32:51]** And if you're constantly telling the leadership,

**[32:55]** the managers, here's how we're measuring it,

**[32:57]** it is changing, we're going from 20% to 60%.

**[33:02]** Like that investment becomes much easier,

**[33:05]** that time investment becomes much easier.

**[33:07]** The reps understand why.

**[33:09]** I think enablement can be sometimes

**[33:12]** it's so important to provide context.

**[33:14]** I talked about that no surprises idea.

**[33:17]** This helps bring down sort of that,

**[33:20]** why am I doing this thing?

**[33:21]** Why is enablement asking?

**[33:23]** You can build that trust over time

**[33:25]** by constantly measuring it.

**[33:28]** - What's been the biggest challenge

**[33:31]** across your career in enablement

**[33:34]** that if you were to give any advice to somebody else

**[33:38]** going down the same path,

**[33:39]** you could maybe help prepare them for.

**[33:43]** - Yeah, I think it really revolves

**[33:45]** around this measurement idea.

**[33:47]** I don't think there's ever been a place

**[33:48]** and I've been at places that have been very sophisticated

**[33:52]** in terms of the way they measure,

**[33:55]** in terms of the RevOps teams that they have.

**[33:59]** I don't think there's ever been a place

**[34:00]** where enablement has had enough

**[34:04]** cache or speed to be able to measure

**[34:09]** the things that they want to measure

**[34:11]** as quickly as they want to measure them.

**[34:13]** And to keep a real beat on that.

**[34:16]** And so I guess what I've learned is you have to be creative.

**[34:20]** You have to find a way to get dirty with the data.

**[34:24]** Enablement isn't always sort of

**[34:26]** come from a background of data.

**[34:28]** They don't come from a background of

**[34:30]** how do these things work?

**[34:31]** How do these revenue systems come together?

**[34:33]** But you've got to find a way to get creative

**[34:35]** to measure those leading outcomes,

**[34:37]** to measure what matters to enablement.

**[34:40]** Because that's the only way that you'll speak to leadership.

**[34:42]** If you can connect those to the revenue outcomes

**[34:44]** that sort of matter to them, that's the only way.

**[34:48]** And so sometimes it's, hey, this data is directional.

**[34:52]** Here's how I found it.

**[34:53]** Here's how I'm measuring time to first deal.

**[34:56]** May not be the perfect way.

**[34:58]** But I'm gonna measure it over time

**[35:01]** and it will change with the business.

**[35:03]** But it is directional.

**[35:04]** And what we're seeing on the other side,

**[35:06]** this correlation, is that these reps are ramping quicker

**[35:10]** than they were before.

**[35:10]** And I measured the before the same way.

**[35:13]** I've had to do this at every single company

**[35:15]** is just scratch my head, get dirty with the data,

**[35:19]** figure it out.

**[35:20]** And I think that becomes not only

**[35:23]** that's been a challenge in my career,

**[35:25]** to find that at different companies

**[35:27]** and have to do that myself.

**[35:29]** I've also found it to be the strongest accelerant

**[35:34]** to my career at each company.

**[35:36]** When I have that voice and I can stand behind the data

**[35:39]** and say, here's how I measured it.

**[35:40]** I know it inside and out.

**[35:42]** I've worked with RevOps.

**[35:43]** Or I figured this out myself

**[35:45]** and it's correlated with what RevOps is doing.

**[35:47]** And these outcomes are showing up in the correlation.

**[35:51]** It's been such an accelerant to what I do,

**[35:55]** both in my career,

**[35:57]** but also in my advancement within that company.

### 36:00 — The enablement data cockpit

**[36:00]** - Let's get specific, 'cause I agree with you.

**[36:02]** Whenever I have had control over the data,

**[36:06]** which I started LeanScale in 2021

**[36:08]** before that I ran RevOps for three companies,

**[36:11]** nothing gave me more influence,

**[36:13]** nothing helped me advocate for my team more

**[36:16]** than having absolute control,

**[36:18]** conviction and confidence in the data.

**[36:23]** As a head of enablement,

**[36:24]** what are those metrics that matter?

**[36:27]** If you had your ultimate data cockpit,

**[36:30]** what are the standard things every enablement person

**[36:33]** should be measuring and monitoring?

**[36:36]** And then maybe what are some of the unique ones

**[36:38]** that may pop up in different scenarios?

**[36:40]** - I'll throw out a couple that I think are really, really fun.

**[36:43]** I've talked a lot about conversational intelligence.

**[36:46]** I think traditionally it's been like,

**[36:48]** are these things mentioned?

**[36:50]** Are we tracking?

**[36:51]** Are they saying these things that we've taught them?

**[36:55]** I think that's a very easy one to measure.

**[36:58]** - The prerequisite for that, I'm curious.

**[37:00]** So you would want to first codify the things

**[37:05]** you want the reps to be talking about.

**[37:07]** And coming up with,

**[37:09]** hey, these are the things that we want to make sure

**[37:11]** are happening on every single call.

**[37:13]** That way you can measure that, right?

**[37:16]** - Yeah, you can do that.

**[37:16]** You can also do it after the fact.

**[37:19]** And it can be a little more ad hoc to your point.

**[37:21]** Sometimes enablement's moving quickly.

**[37:23]** You get something out the door.

**[37:24]** What's great about sort of a lot

**[37:26]** of these conversational intelligence tools

**[37:28]** is you can look back.

**[37:29]** You can scratch your head and you say,

**[37:31]** these were the things we were training on,

**[37:33]** codifying those.

**[37:35]** And let's look back and see,

**[37:37]** was that happening before, to what degree?

**[37:39]** And what's happening now?

**[37:41]** I think when it comes to sort of like

**[37:43]** sales methodology behaviors,

**[37:44]** absolutely, yes, you're so spot on, Anthony.

**[37:47]** Yes, we need to codify those,

**[37:49]** plug those into these systems and say,

**[37:51]** over time, what's happening?

**[37:53]** With the ways that we're asking reps to go to market.

**[37:56]** So that's certainly one is measuring at that level.

**[38:00]** Where I found some other interesting areas to measure

**[38:04]** is Slack, I think a lot happens in Slack.

**[38:07]** One thing I've measured in my career is like,

**[38:10]** we roll something out, there's confusion.

**[38:13]** I'm measuring like the number of repeat questions.

**[38:17]** And now with AI, you can ask your LLM,

**[38:20]** like how often in this channel

**[38:23]** are we seeing repeat questions show up

**[38:25]** or questions that are similar?

**[38:27]** You run a training and you say,

**[38:29]** now are these repeat questions continuing to happen

**[38:32]** at the same rate that we had before?

**[38:35]** I think that's a really interesting barometer.

**[38:37]** It's a very interesting barometer

**[38:39]** for the subject matter experts

**[38:40]** who are answering in that channel.

**[38:42]** You can reduce that by running a training and say,

**[38:44]** by the way, I've made your job a little bit easier.

**[38:47]** You're not answering the same level of questions,

**[38:49]** but for the field as well,

**[38:51]** they're now asking questions

**[38:53]** and I've seen this trend happen at multiple companies.

**[38:55]** When you reduce the repeat questions

**[38:58]** in Slack and email and Jira, wherever,

**[39:00]** you start to see that the questions become

**[39:02]** much more deal specific, much more nuanced.

**[39:05]** And to me, that's a sign that like,

**[39:07]** hey, you've done the foundational training.

**[39:10]** Folks have the sort of common understanding

**[39:13]** about the different things that you need to do,

**[39:16]** but they are asking much deeper questions.

**[39:18]** They're thinking about these problems

**[39:20]** at a much deeper level,

**[39:21]** which is what you want them to be doing.

**[39:23]** - Those make a lot of sense.

**[39:24]** I'm wondering if there are any other measurements

**[39:27]** that you wanna make sure you're capturing

**[39:29]** for your enablement cockpit

**[39:31]** and also the ones that are articulating value

**[39:33]** for enablement as well.

**[39:35]** - Yeah, I'd like to tell a story just like,

**[39:38]** I think it's important to be measuring sort of how,

**[39:43]** from a competitive lens, how are things landing?

**[39:46]** I think nowadays there's probably a weirder competitive lens

**[39:50]** for a lot of companies that are kind of upstarts

**[39:52]** where the competitor is billed versus buy.

**[39:56]** And so that becomes a new unique area to lean in,

**[40:00]** especially for some of the AI native companies.

**[40:02]** But when I measured competitive win rates

**[40:05]** as a part of that win-loss program,

**[40:07]** that was something we did quarter in and quarter out.

**[40:10]** Here's our top five competitors.

**[40:12]** Are we seeing them show up in deals?

**[40:14]** And this was like pre-gong, pre-anything.

**[40:18]** This was pretty dirty spreadsheet that we were running,

**[40:20]** but we had a sales kickoff coming up

**[40:23]** and the initial direction was like,

**[40:25]** let's just do more sales training.

**[40:28]** But because we were measuring this competitive win rate,

**[40:30]** I saw over time that we had this persistent decline

**[40:34]** against two of our biggest competitors.

**[40:36]** And I think maybe this is a key insight for enablement too,

**[40:39]** of bringing programs forward based on that data.

**[40:43]** But I was able to sort of bring this data to our CRO

**[40:45]** and say, hey, this isn't just an isolated event.

**[40:49]** This is a trend, a pattern we've seen

**[40:51]** across successive quarters.

**[40:53]** Is there something we can do at kickoff

**[40:55]** that focuses here?

**[40:57]** And because I had the data,

**[40:59]** we were able to sort of make that case.

**[41:02]** And what we did was we did sort of this,

**[41:05]** peer-to-peer training at sales kickoff.

**[41:07]** We had some reps come up,

**[41:09]** talk about what they'd done, what they'd done differently,

**[41:12]** or even just their process for beating these competitors.

**[41:16]** And sometimes it's so helpful to have reps speak out.

**[41:20]** They're learning themselves like,

**[41:21]** oh, hey, I did this thing kind of well.

**[41:24]** I should probably replicate that on my own deal.

**[41:26]** Like enablement can sometimes be the teach back,

**[41:30]** but it also makes it more attainable for the field.

**[41:32]** I think like sometimes it's so hard

**[41:35]** to kind of like picture this training as helping me.

**[41:39]** But if you have a rep speaking to that,

**[41:42]** it really can put it in the sort of lens of,

**[41:45]** oh, I can do this too.

**[41:46]** This is attainable, this is achievable.

**[41:48]** The long way to say like, after this training,

**[41:51]** we watched the competitive win rates

**[41:54]** against those two competitors.

**[41:56]** We focused on our top two.

**[41:58]** And that following quarter,

**[42:00]** we saw our win rate go up 10 points

**[42:03]** against one competitor and 15 points another.

**[42:06]** And this wasn't a competitor

**[42:07]** that we were competing against one, two times.

**[42:11]** So your point of like that incremental change

**[42:14]** being a huge outcome.

**[42:15]** We had six figure sort of ACV deals,

**[42:19]** or our ACV was about six figures

**[42:22]** or in the six figure range.

**[42:23]** So that change, that 10 to 15 point percentage change

**[42:28]** made a huge impact on what we were doing,

**[42:32]** what we were bringing in,

**[42:33]** but it also gave enablement again,

**[42:35]** sort of that further momentum and that cache to say,

**[42:38]** here's the data that I saw, here's what we did,

**[42:41]** and here's the outcome.

**[42:43]** Now let's do more.

**[42:45]** - And let me remind anyone listening,

**[42:46]** that's without adding another rep,

**[42:49]** without adding product capabilities,

**[42:52]** without doing more marketing,

**[42:54]** without making another dollar investment anywhere else,

**[42:59]** those gains are massive.

**[43:01]** So I think just especially once the team is at scale,

**[43:06]** these yield changes,

**[43:09]** these yield shifts can mean millions and millions of dollars

**[43:13]** and really getting your team efficient

**[43:16]** and running really, really well.

**[43:18]** - I have a question 'cause I think this is probably

**[43:22]** one of the most misconstrued aspects of hiring

**[43:27]** and bringing salespeople in.

**[43:29]** There's this concept of ramp,

**[43:31]** and people will throw out the term,

**[43:33]** well, when are the salespeople gonna be ramped?

**[43:35]** And I think a lot of people have

**[43:36]** a million different definitions for what that is.

**[43:41]** From your perspective as an enablement professional,

**[43:44]** what does a fully ramped salesperson mean

**[43:48]** and how do you get them there?

**[43:50]** - Yeah, I think you gotta see the behaviors.

**[43:53]** You gotta see someone who's,

**[43:55]** you take a look at what reps are consistent

**[43:58]** quarter in, quarter out.

**[44:00]** They're showing the same sort of output consistently,

**[44:04]** which sometimes at some companies can be very easy to see

**[44:09]** because not a lot are doing that.

**[44:11]** They have these bumps and lumps.

**[44:12]** So it's looking at that and then it's spending time

**[44:15]** understanding what are the behaviors that sit behind that?

**[44:18]** How often are they on the phone?

**[44:21]** How much are they self-sourcing to create their own pipeline?

**[44:24]** What are they doing from sort of a brass tacks

**[44:28]** foundational perspective?

**[44:31]** And you're looking to see what do their calls look like?

**[44:35]** Are they following these certain behaviors

**[44:36]** that we've agreed upon?

**[44:38]** And it's maybe tweaking some of the processes that you have,

**[44:41]** then it's enabling to that and you spell that out.

**[44:44]** You say, very clearly in the onboarding,

**[44:47]** this is what top reps do.

**[44:49]** Here's the data.

**[44:51]** This is what you're expected to do.

**[44:53]** This is how you're expected to inspect your own pipeline.

**[44:56]** This is how you're expected to re-qualify.

**[44:59]** Week in, week out, this is how you're expected to run

**[45:03]** the give get sort of conversation throughout the process

**[45:06]** from day one to the end of a sales cycle.

**[45:10]** So I think it's looking at those behaviors

**[45:12]** and then working back.

**[45:13]** I also think it's really important to work

**[45:15]** with the leadership and understand

**[45:17]** what is time to first deal?

**[45:19]** What does ramp look like to them?

**[45:21]** Because you can come up with as many metrics as you want

**[45:24]** or any sort of framework, but if it doesn't land for them

**[45:27]** and there's not sort of a consensus or agreement

**[45:30]** at that level, you're always gonna get into

**[45:33]** sort of these knife fights at the end.

**[45:35]** And I've seen different measures,

**[45:37]** different measures of what time to first deal looks like.

**[45:40]** And then one other thing that I've done

**[45:43]** and I think is a really interesting way to look at this

**[45:45]** is sort of a leading metric to that

**[45:50]** is not looking at time to first deal,

**[45:52]** but looking at time to fourth or fifth deal.

**[45:55]** Are the reps creating momentum?

**[45:57]** And that can be an early flag, early signal

**[45:59]** to those managers where you can provide intervention

**[46:03]** at that stage if you're not seeing that period of time

**[46:07]** accelerate happen within sort of the window

**[46:10]** that you would expect.

**[46:12]** And you're not just looking at time to first deal

**[46:13]** and saying, great, they close their first deal.

**[46:15]** But what momentum are they creating?

**[46:17]** And I have found once they sort of break the seal,

**[46:20]** they can start creating their own momentum.

**[46:23]** But if something wobbles within that sort of first few deals,

**[46:28]** you can provide intervention and make sure that

**[46:31]** they are on track to achieve the behaviors

**[46:33]** that you want them to achieve for a fully productive rep.

**[46:38]** - Let me rephrase what I'm not hearing.

**[46:41]** Ramp does not mean they're trained on the product

**[46:44]** and ready to do a demo.

**[46:46]** - Yeah, yeah, yeah.

**[46:48]** - Which I think a lot of people are like,

**[46:50]** train them on the product, walk through the pitch deck,

**[46:54]** they're ready to go.

**[46:55]** First one, two weeks, lock and load.

**[46:57]** We have a ramped rep and it's like, no, no, no, no, no.

**[47:00]** There is so much more that goes into it

**[47:02]** before you have confidence that this person can reliably

**[47:06]** and continuously hit their quota and produce for you.

**[47:09]** - Yeah, I think I'll just add one more note to that.

**[47:13]** When I found the most success in thinking about onboarding,

**[47:17]** it's not, to your point, shoving a bunch of stuff at them

**[47:21]** and saying, this is the latest and greatest,

**[47:22]** go figure it out.

**[47:24]** It's building it around the sales process

**[47:27]** so that a rep knows, okay, I got a deal.

**[47:29]** What do I do next?

**[47:30]** And you create this sort of like,

**[47:32]** you orient and you speak their language, frankly,

**[47:36]** for how they think about their work.

**[47:39]** When you orient the onboarding program process

**[47:44]** around the sales process or the sales journey,

**[47:47]** it becomes much easier for them to quickly recall,

**[47:50]** oh, this is what I learned about,

**[47:54]** what I need to do with an SQL.

**[47:56]** Or this is how the process happens

**[48:00]** when I move it to propose.

**[48:02]** These are the resources that I need during this.

**[48:04]** This is the actions, the behaviors, the exit criteria

**[48:07]** that I need to achieve.

**[48:09]** It gives them sort of that lens to be able to recall,

**[48:13]** which is so important 'cause they're drinking

**[48:14]** from the fire hose at that first few weeks.

**[48:19]** And if you can orient them,

**[48:20]** that awareness pays off in dividends.

**[48:25]** - I think it's an excellent frame of reference

**[48:28]** that you have for describing how to get somebody to ramp.

### 48:32 — AI role play: stretching before the sprint

**[48:32]** This would not be a podcast in 2026 if I didn't ask you,

**[48:37]** how are you leveraging AI in enablement?

**[48:41]** And what is the most modern approach to enablement today?

**[48:47]** - Well, gosh, it's changing every day.

**[48:50]** There's more capabilities.

**[48:52]** There's more things I'm like hearing about,

**[48:54]** learning about, have access to.

**[48:57]** I'm doing some really interesting analysis

**[49:00]** by connecting to a lot of our data sources,

**[49:02]** our data warehouses to really analyze call data,

**[49:06]** understand how that's happening outside

**[49:08]** of some of the systems that we've traditionally used.

**[49:11]** In my old win-loss days when I had a spreadsheet

**[49:14]** and I was downloading it and running pivot tables,

**[49:16]** this was like the pipe dream and I'm now living it.

**[49:18]** So it's so much fun.

**[49:20]** And I would say like to anybody who's in enablement,

**[49:23]** like just get out there, explore, try new things,

**[49:26]** get creative.

**[49:27]** But the thing that I've seen kind of come online recently

**[49:31]** and a lot of companies are leaning into it,

**[49:33]** and I think it could be really, really interesting,

**[49:35]** is sort of this sense of role play.

**[49:38]** There are now ways and companies that are running,

**[49:43]** that have these platforms that are ingesting a ton of data,

**[49:46]** a ton of like methodologies, your own methodologies,

**[49:50]** your own call data to prepare for calls.

**[49:55]** And this could be anyone from a rep to an SDR

**[49:59]** to even CS running QBRs.

**[50:02]** And I think this idea of being able to practice

**[50:05]** outside of live deals.

**[50:09]** And we all know how critical it is to close live deals

**[50:11]** right now in 2026.

**[50:13]** Like you don't want to be wasting your pipeline,

**[50:16]** sort of figuring it out.

**[50:17]** This comes, you know, this goes

**[50:18]** to our onboarding conversation.

**[50:20]** Like you want reps to be able to practice multiple times

**[50:23]** and work out the kinks.

**[50:25]** And then you want to create the behavior

**[50:27]** where reps are doing this, you know, prior to calls.

**[50:30]** They understand the call they're going into,

**[50:32]** and they're able to practice just like you would

**[50:35]** for a big speech, right?

**[50:36]** You would practice, you know, with someone.

**[50:40]** You'd look in the mirror, you'd practice that.

**[50:42]** And I think the opportunities to do that now with AI

**[50:45]** are so critical.

**[50:46]** I had a sales leader who said, you know,

**[50:48]** this is the same thing as like stretching

**[50:51]** and working out the hammies before you go for,

**[50:54]** you know, a sprint.

**[50:55]** And I'm really sort of excited to see where this space goes

**[50:58]** and how realistic it can get

**[51:00]** and how forward thinking it can get, you know,

**[51:02]** bringing in, you know, the calls that are already

**[51:05]** on your calendar and prepping you

**[51:06]** for those specific personas, those specific transcripts.

**[51:10]** I think that can be a really exciting area.

**[51:13]** And once reps sort of see the value of it,

**[51:15]** I think it is a new space, so it's challenging.

**[51:17]** I think the ones who will succeed

**[51:19]** are the ones who are leaning into that practice.

**[51:21]** And we're already seeing it here of who me,

**[51:23]** the ones who are doing that are our top performers.

**[51:27]** And they are our top performers because they're still hungry.

**[51:30]** They still have that chip on their shoulder

**[51:32]** to make this happen, to get out there, to be resourceful,

**[51:35]** to take every opportunity to get better

**[51:38]** and sharpen that axe every day.

**[51:40]** Well, I think it's a really exciting time to leverage AI.

**[51:43]** And especially in the role-playing sense,

**[51:44]** I mean, I've never done a presentation

**[51:47]** or walked into a big meeting without doing a dry run.

**[51:51]** And I think being able to do dry runs at scale

**[51:54]** because you don't need a loop in a million people

**[51:56]** in order to do it effectively,

**[51:58]** I think is gonna be fantastic.

**[52:00]** And like you said, the reps that take advantage of it

**[52:02]** will show in their performance.

### 52:06 — Wrap

**[52:06]** But Chad, thank you so much.

**[52:08]** This has been an absolute masterclass in enablement.

**[52:12]** I think it's one of the most misunderstood parts

**[52:15]** of operations and go-to-market

**[52:18]** and exactly what does good look like in here.

**[52:20]** And I think you've laid out a really, really strong roadmap

**[52:23]** first showing how to lay the groundwork

**[52:26]** to get the data that you need to make decisions

**[52:29]** and advocate for the proper amount of resources

**[52:31]** that you need to do a good job.

**[52:33]** So we're looking at increasing the yield,

**[52:35]** whether it's conversion rate, ACV, moving velocity,

**[52:39]** moving things through the funnel quicker.

**[52:41]** And as we mentioned, small increments and improvement

**[52:44]** can have massive outsized gains

**[52:47]** and the equation also runs the other way.

**[52:50]** So this is not only in an area to invest in

**[52:54]** just for opportunities,

**[52:56]** but also to mitigate downside risk as well,

**[52:59]** especially as you're growing and scaling.

**[53:01]** You're gonna be adding tens and tens of reps

**[53:04]** as you're growing, as you're building fast.

**[53:07]** And it requires a lot to get one of those reps

**[53:10]** ramped and onboarded.

**[53:12]** And again, ramping does not mean

**[53:14]** they're trained on the product.

**[53:15]** It means they're predictably reliably closing deals,

**[53:18]** hitting their quota, producing at the rate

**[53:20]** you expect them to.

**[53:21]** So Chad, just thank you for everything here,

**[53:24]** excited for people to listen,

**[53:26]** excited for this to be on LeanScale's MCP

**[53:28]** so people can query anything from the conversation.

**[53:31]** And I can't wait to see what you do next.

**[53:36]** - Oh, well, thank you, Anthony.

**[53:37]** This has been so much fun.

**[53:38]** I love that the enablement worlds

**[53:41]** and the RevOps worlds are coming together

**[53:43]** in this conversation.

**[53:44]** I think that's where this space is going.

**[53:47]** And I love that we get to talk about it

**[53:49]** and you can tell I'm super passionate about it.

**[53:51]** So I wanna see these worlds come together more

**[53:54]** and this is a perfect opportunity for that.

**[53:56]** And like I said, this has been such a fun,

**[53:58]** thoughtful conversation.

**[53:59]** So thank you for your questions.

**[54:00]** And if anybody out there has any questions for me,

**[54:03]** like I love this stuff.

**[54:05]** It is so fun to talk about

**[54:06]** and learn from the community of RevOps and enablement.

**[54:11]** So always feel free to reach out.

**[54:13]** I'm happy to chat at any point.


---

_LeanScale Knowledge Hub. Free to quote and cite with attribution to The LeanScale Podcast (https://www.leanscale.team)._